OREO Cupcakes and Cookies and Cream Frosting

Whip up a batch of these heavenly chocolate cupcakes and homemade cookies n' cream frosting for someone who loves OREO sandwich cookies! This recipe creates fluffy, decadent cupcakes that have a great texture.

Many of you may remember that Adam left his job at Apple Inc. A few months ago, he started his job working as an IT assistant at a school in Phoenix, and a few weeks ago, he was promoted to an IT manager position and he has already become an essential team member to their department. It is so wonderful to see him actually enjoying his work, because seeing Apple work him so hard and never give him anything to show for it was frustrating for me since I saw the toll it was taking on him.

This new-but-not-so-new job of his has already made him much happier every day, and he has expressed to me that he really enjoys working for a school and he enjoys hanging out with his co-workers. A few days ago, Adam came home from work and told me that we were invited to one of his superiors' homes over the weekend for a friendly poker night with some of the other employees from the school. 

He told me that he needed to bring some food and drinks to the party, and even though I had already packed up all of my baking supplies just a few days ago, I knew I needed to dig out the freshly-packed moving box and whip up a batch or two of homemade cupcakes for the poker night with his co-workers. Admittedly, it has been a while since I have done any baking with traditional flour, sugar, or cookies. Since we started adapting to a ketogenic diet back in March, I have switched to ingredients like almond flour and other low-carb and low-sugar substitutes. But being that this party was with his co-workers and one of his superiors was hosting the party, I knew I had to pull out the yummier ingredients and make these decadent, showstopper OREO cookie cupcakes. 

These cupcakes are packed with OREO cookie chunks and chocolate chips, piped with vanilla frosting inside, and then decorated and topped with homemade cookies and cream frosting made with OREO cookies!

As I mentioned, since I have not been baking for a while with traditional baking ingredients since they are not ketogenic diet-friendly, I opted to do a recipe hack and bought a box of triple chocolate cake and then packed it with some extra ingredients to really give it a rich flavor and texture. 

Normally I would prefer to make the cake completely from scratch, but this time around, I opted to not stock up on loads of flour and sugar that I would not use again (since they are not keto) and just amped up a box of store-bought boxed cake. 

For those wondering, this is a replicate of a 1918 vintage, OREO cookie sandwich tin that I found while I was thrift shopping. I paid a dollar or two for it, and I absolutely adore it! Although I do not use it to store cookies, I do keep an assortment of my piping tips and other frosting accessories inside of it. 

OREO Cupcakes and Cookies and Cream Frosting
*yields 30 cupcakes, yields frosting for 30 cupcakes

OREO Cupcakes Ingredients:
  • 10 OREO cookies, crushed
  • 1 box of triple chocolate cake mix (15.25 ounces)
  • 1 box of instant chocolate pudding mix (3.7 ounces)
  • 3/4 cup of chocolate olive oil (vegetable oil is also a suitable oil)
  • 1 cup of sour cream
  • 4 eggs
  • 1/2 cup of hot water
  • 1 cup of semi-sweet chocolate chips
  • 16 ounces of white vanilla frosting

Cupcake Directions:
  1. Preheat the oven to 350 degrees and line a cupcake baking pan with cupcake liners.
  2. In a large mixing bowl, combine the chocolate cake mix and the chocolate pudding mix.
  3. Pour the olive oil and the sour cream into the bowl and mix well. 
  4. Crack an egg into the bowl and mix it in. Then continue to add in the eggs one at a time and mix. 
  5. Pour in the hot water and mix. 
  6. Add in the crushed OREO cookies and semi-sweet chocolate chips and mix them into the cupcake mix so that they look evenly distributed.
  7. Fill the cupcake tins only half way up, and then bake the cupcakes in the oven at 350 degrees for 16-17 minutes. Test the cupcakes at about 14-15 minutes by inserting a toothpick into the center. If the toothpick comes out clean, remove the cupcakes from the oven and allow them to cool.
  8. Finally, when the cupcakes have completely cooled, pipe a small amount of white frosting into the center of each cupcake using a frosting bag and a small piping tip. Repeat until you have added frosting into the center of each cupcake.

Cookies and Cream Frosting Ingredients:
  • 15 OREO cookies
  • 1 cup of salted butter, room temperature
  • 3 cups of powdered sugar
  • 1 teaspoon of vanilla extract
  • 2 tablespoons of heavy whipping cream

Frosting Directions:
  1. Before frosting cupcakes, allow them to cool completely to the touch (and then some). 
  2. To prepare the frosting, use a large mixing bowl to mix the butter and the powdered sugar together about 1/2 cup of sugar at a time. Repeat this until all of the sugar is blended into the butter. 
  3. Add in the vanilla extract and the heavy whipping cream and mix well.
  4. Pulverize the OREO cookies either in a blender or food processor, and then add them into the mix well. 
  5. Pipe the frosting onto the cupcakes, and then decorate however you want or serve to enjoy. 

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  1. I would eat so many of these cupcakes. They look fabulous! Plus I'm a fan of OREOS, so this is a perfect combo for me.

  2. So much you can do with Oreos! These look absolutely delicious! I totally need to try and make some of these myself.

  3. Oh. My. God. You just become my hero for life. FOR LIFE! I'ma huge Oreo fan, and I love cupcakes. I think this might be the most amazing cupcake recipe I've ever seen.

  4. My son just asked for an Oreo cake for his birthday, but I may need to try these instead!! I think they will be a big hit!

  5. Anything with oreos in it has got to be delicious!

  6. Those look like quite an inviting treat! I know they have some oreo look-alikes that are gluten free for we celiac folks. I think they're so pretty!

  7. I love Oreo's!!! I buy the ice cream, the cookies but have never had an Oreo cupcake! This looks so easy and delicious. I will try and will tag you when I make 'em.

  8. OMG these sound to die for! Cookie and creme is one of my favorite flavors of dessert . . . might have to make these for my next birthday.

  9. I loooove oreos! I'm always looking for a new way to sneak them into a dessert. These look delicious!!

  10. Wow! These look like a wonderful treat! I love oreos and making cupcakes with them, just expands on their goodness. I too am familiar with companies working people into various states of unhappiness. We moved recently and my husband now works for a much better place and is a lot happier these days!

  11. Now you are speaking my language. Oreo anything is my favorite!

  12. We are all huge Oreo fans in our household. These look delicious and fun to make. I'll have to make these with the kids as a treat.

  13. Oh, my kids would go NUTS for these! We just can't get enough OREOS! BTW that vintage tin is adorable!

  14. I’m a HUGE Oreo fan - how can you not be?! I bet these are delicious. They would be a hit with my kids!!

  15. Oh my! Now that I am celiac and can't eat Oreos I continually crave them! These look so scrumptious.

  16. What a great treat to bring to someone's get together! So glad to hear he's enjoying his work -- that's awesome (like these cupcakes)!

  17. My husband would love these. I am going to have to try to tackle them so he can bring a treat to work.

  18. This is the perfect combo! My kids love Oreo and Cookies Cream! Clever recipe! Love it!

  19. I love oreos so I am going to have to make some oreo cupcakes!

  20. What an awesome dessert idea! Oreo's always go over well!

  21. I would love to have some of these! These are some amazing treats!

  22. Okay, those cupcakes look heavenly! Anything with Oreo in it, and I'm in.

  23. Because of food allergies we often have to take a cupcake we've made at home for our kids to eat at parties and other types of gatherings. So always appreciate seeing new and interesting cup cake recipes. We love Oreos!

  24. Umm, these are beautiful! Not to mention, I bet they are delicious! Bookmarking to make these! Thanks so much.

  25. We love baking at home! I think my daughter would love to bake these together. It's a combination of her favorite, chocolate and oreos.

  26. Oh yeah! These look delicious. I was just craving some Oreo or cookies and cream ice cream last night. It would go well with this.


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